Acetic Anhydride → HCID 22990193, compound

HRID 1169376Notes

Reaction equation

HRID 1169376 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C1COCC1>[CH3:1][N:2]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:24](=[O:26])[CH3:25])=[CH:15][CH:16]=1)[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine

Product 1

HCID 22990193HCID 22990193, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (551 mg) in THF (50 ml) were added triethylamine (0.42 ml) and acetic anhydride (0.26 ml), and the resulting mixture was stirred at room temperature for 3 hours. After evaporation of THF, the residue was extracted with ethyl acetate. The extract was washed successively with an aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to obtain N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]acetamide (472 mg) as light yellow crystals.

Workup

  1. customAfter evaporation of THF
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed successively with an aqueous solution of sodium bicarbonate
  4. dry with materialan aqueous solution of sodium chloride, was dried with anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-797de204f80b4e55ba849401deff2cb9
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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